Wikipedia talk:WikiProject Chemistry/Archive 55

This is an archive of past discussions on Wikipedia:WikiProject Chemistry. Do not edit the contents of this page. If you wish to start a new discussion or revive an old one, please do so on the current talk page.

Archive 50

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Archive 53

Archive 54

Archive 55

Sciencemadness.org

An insource search shows that we currently have 70 cases where Sciencemadness.org has been used in chemistry articles. Some uses (e.g. in Copper(I) phosphide, current citation #6) have that wiki as a source for our Wikipedia article, although Sciencemadness itself usually does not cite any sources and is clearly not reliable by our standards. More worryingly, it seems that many of the instances of links to that website are to books and articles which are copyright. For example, Tetrafluorohydrazine has a citation #3 to John Drury Clark's 1972 book "Ignition" with a link to a scanned copy as a .pdf. I think we need to go through all 70 instances and either remove the cite or, if the cite itself is valid, remove the links to the copyvio. Comments? Mike Turnbull (talk) 14:29, 28 May 2024 (UTC)

Support Pygos (talk) 15:07, 28 May 2024 (UTC)

I've changed the Tetrafluorohydrazine citation to point to the Google Books preview rather than Sciencemadness.org. I can probably do the same with a lot of these links. Recon rabbit 15:22, 28 May 2024 (UTC)

Thanks, User:Reconrabbit. I was intending to do similar but was waiting a bit to see if anyone had reasons not to do that. Mike Turnbull (talk) 15:27, 28 May 2024 (UTC)

Support replacing those links. A number of dubious sources are cited in our articles, so it is a good idea to root them out. Educational sites include Khan Academy (https://www.khanacademy.org/science/organic-chemistry) and ChemLibre (https://chem.libretexts.org/Bookshelves/Organic_Chemistry) seem to present legitimate information, but they probably are not reliable sources. The overarching problem is that most good content sits behind paywalls.--Smokefoot (talk) 15:48, 28 May 2024 (UTC)

That's a good point. Editors here who write chemistry articles should have access to paywalled sources either through their institution or the Wikipedia Library, for example. Provided we summarise such sources accurately, it doesn't matter that the average reader can't themselves easily read the sources. We must try to write quality articles and that often means citing specialist publications. Mike Turnbull (talk) 17:36, 28 May 2024 (UTC)

Chemistry LibreTexts is a tricky one out of these; the attribution is terrible, but I have included them as references on some topics because I have had trouble finding online sources that define in basic terms specific concepts like crystal field excitation. Recon rabbit 16:02, 28 May 2024 (UTC)

In the spirit of gaining some consensus on on-line sources, another one is American Elements (https://www.americanelements.com). Dozens or hundreds of chem articles cite this website. Maybe someone can comment on their status as an RS. Like Sigma-Aldrich or other vendors, their physical data are probably acceptable. But they dress up their articles with a narrative, which is not verifiable and is not reviewed in any way. Their narratives are window dressing for the products that they are selling.--Smokefoot (talk) 22:49, 28 May 2024 (UTC)

I support not using American Elements for "use" verification, as we cannot see where their info came from, and when trying to confirm, perhaps only one researcher tried that application. Graeme Bartlett (talk) 00:01, 29 May 2024 (UTC)

Contents from American Elements may contain original research. --Leiem (talk) 15:08, 29 May 2024 (UTC)

Sciencenotes.org is another site that shows up infrequently and is written largely by two people with scientific backgrounds but no oversight. Recon rabbit 23:43, 28 May 2024 (UTC)

I have now replaced or removed all but one reference to Sciencemadness.org. Graeme Bartlett (talk) 01:36, 29 May 2024 (UTC)

Thanks for doing that heavy-lifing! DMacks (talk) 02:24, 29 May 2024 (UTC)

@Graeme Bartlett:Thanks for removing the direct Sciencemadness.org cites. The insource search at the top of this thread is still giving 62 hits which are copyvios IMO. I'll start trying to replace them, and User talk:Reconrabbit will probably assist. Mike Turnbull (talk) 10:17, 29 May 2024 (UTC)

Use in Nicotine and pyridine is not a copyvio, as works are in public domain. Graeme Bartlett (talk) 12:46, 29 May 2024 (UTC)

OK, I'll check as I go. Mike Turnbull (talk) 13:36, 29 May 2024 (UTC)

There are also several US government publications which are in the public domain. Though I am not sure about LANL publications: are they government or not? Graeme Bartlett (talk) 04:48, 1 June 2024 (UTC)

I think the LANL ones are OK. Part of the website says that's where those documents originally came from. Their library has many books that are clearly PD owing to age but also quite a few I would consider to be copvio as too recent. Anyway, those linked from cites in our articles has been trimmed down to the extent where I'm giving up on the final ones. Mike Turnbull (talk) 11:04, 1 June 2024 (UTC)

Sources

Ok, maybe we transition to a related topic. If one does not have access to basic textbooks, it is next to impossible to edit technical content. "Crystal field excitation" is not a term encountered very often. Yes, one can imagine what it is, but the phrase is not indexed in usual textbooks (Wiberg, Cotton&Wilk, Shriver). My somewhat obnoxious point is that if one is struggling to find a source for a topic, maybe that topic does not merit an article. --Smokefoot (talk) 17:23, 28 May 2024 (UTC)

Ninovium

I just found ninovium article. I think this article should either be merged with Victor Ninov or with oganesson. Could somebody please take a look? ReyHahn (talk) 13:26, 15 May 2024 (UTC)

It is probably better merged with Ninov's article, since the fraud has become a pretty defining event of his career; for oganesson, it would be a history subsection at most.

Certainly doubt it merits its own page, especially under the current name - and especially one that introduces it as "a synthetic element", and says things like "ninovium's existence as a valid element remains unsubstantiated, and its characteristics remain uncertain" - which makes me wonder if the page's author understands that the claimed "ninovium" necessarily is oganesson. The whole incident could warrant something like element 118 falsification scandal, I suppose?

I would say redirect "ninovium" to oganesson#Unconfirmed discovery claims, while integrating the salvageable parts of the existing article into Ninov's? Fishsicles (talk) 18:28, 7 June 2024 (UTC)

Categories for Fiveling

There is a dispute between me and the article creator about how broad the categories for this article should be. See Talk:Fiveling#Intractable dispute over categories. –LaundryPizza03 (d c̄) 22:50, 10 June 2024 (UTC)

Pro-forma, please note that @LaundryPizza03 did notify me that he is cross-posting. Ldm1954 (talk) 02:05, 11 June 2024 (UTC)

Removing some Hindawi refs?

Apparently Hindawi (publisher) is a huge operation, occasionally putting out some controversial journals. Here are some that appear to apply to the Chemistry project:

Advances in Materials Science and Engineering
Biomed Research International
Contrast Media & Molecular Imaging
Disease Markers
Evidence-Based Complementary and Alternative Medicine
Journal of Environmental and Public Health
Journal of Healthcare Engineering
Journal of Nanomaterials
Oxidative Medicine and Cellular Longevity

According to Retraction Watch the above journals (and others) have been "delisted" from Web of Science. So, I started to remove some of these references from chemistry articles. Are my removals a good idea?--Smokefoot (talk) 04:19, 13 June 2024 (UTC)

I think it would be a mistake to just remove the citations. Just because some indexer thinks a journal is lower quality, does not mean that an article in it is low quality. We'll probably need to replace by another reference if we take them out. I see usage in some broad topics that would easily be replaceable for important facts. Otherwise if the referenced text is garbage based on a garbage publication, then it should be removed altogether. So we should examine each use. {However I have deleted a chemical referenced to Journal of Nanomaterials from an article I wrote (as substance not well proved to exist) }. Graeme Bartlett (talk) 07:32, 13 June 2024 (UTC)

OK, I undid my edits. --Smokefoot (talk) 16:51, 13 June 2024 (UTC)

Helium Featured Article review

This discussion may be of interest to the community here. XOR'easter (talk) 20:35, 17 June 2024 (UTC)

RfC on meaning of nonmetal

There is a RfC on this topic at Talk:Nonmetal#RfC_on_meaning_of_nonmetal which may be of interest. Is the primary use of the term nonmetal for elements in the periodic table, see discussions in Talk:Nonmetal and also at Talk:Nonmetallic compounds and elements. Editor Sandbh is arguing that this is the case, with some other additions. Editors Johnjbarton, Ldm1954 and YBG have questioned this, and both Johnjbarton and Ldm1954 have questioned the scientific accuracy.Ldm1954 (talk) 07:46, 18 June 2024 (UTC)

Op-Ed: Runnin' blind

It is nearly impossible to write an overview of a topic without good sources. It can also be a disservice because the topic might be misrepresented. If one does not have access to the major works in an area, ask for help, pray that Google books gives you a glimpse to the good stuff, or forget the writing project because you will be forced to rely on old-timey literature and junky online stuff. Almost all the good on-line content is behind a paywall or is inside of major textbooks and encyclopedias. Some major works are online as pdf's, possibly illegally. March's Organic Chem is one example, Greenwood and Earnshaw for Inorganic (especially Main Group) is another. The major review journals (Chem Soc Rev, Angew, Chem Rev) have some open-access content. Org Syn is open access, but it does not provide sufficient context for an overview. --Smokefoot (talk) 13:32, 23 June 2024 (UTC)

McMurry's Organic Chemistry is now free-access online. DMacks (talk) 14:46, 23 June 2024 (UTC)

Yes, at Openstax, (at 193 Mb) which also has several other useful textbooks. Mike Turnbull (talk) 14:51, 23 June 2024 (UTC)

All true. One recent welcome trend is for authors of "the good stuff" to make it open access. A recent example is Peter Atkins making the latest version of Concepts in Physical Chemistry freely available and even downloadable at doi:10.1039/9781837674244. I've added that link to our article about him and would encourage anyone to use this to update relevant topics. In a related move, IUPAC have licensed their Gold Book CC BY-SA 4.0 which has allowed User:Walkerma to include their definitions unchanged into articles such as adsorption and Boltzmann constant. Fortunately, many good review articles are available via University subscriptions to journals, which is how some of our student editors will gain access. Others can reach JSTOR via the Wikipedia library. My pet peeve is that the American Chemical Society don't seem to provide better access via that or other similar mechanism. Mike Turnbull (talk) 14:46, 23 June 2024 (UTC)

Maybe we should assemble a list with links on our project page?--Smokefoot (talk) 15:01, 23 June 2024 (UTC)

Good idea, which I see you have begun to do. We just need to ensure that no-one adds a WP:ELNEVER to a copyvio version of something. Mike Turnbull (talk) 15:56, 23 June 2024 (UTC)

It would be great if Chemical & Engineering News was easier to access beyond the first "free article"; their online archives are extensive. Could be a proposal for WP:TWL? Recon rabbit 16:40, 23 June 2024 (UTC)

Its an ACS magazine, hence that problem. However, if you know the URL (from their website) that you want, you can often find it archived at the Wayback Machine etc. So, for example, this one . How this squares with WP:ELNEVER I leave to the lawyers: safest would be to use the information you find to write your Wikipedia entry and cite it but not link it. Mike Turnbull (talk) 17:01, 23 June 2024 (UTC)

I don't imagine it would be different from any other situation where we link to paywalled articles. I did some digging and found a discussion on the External Links noticeboard that is tangentially related: Wikipedia:External_links/Noticeboard/Archive_25#Potential license laundering through ghostarchive.org Recon rabbit 17:52, 23 June 2024 (UTC)

I am guilty of sometimes citing refs that I cannot access. The usual scenario is that I'm reading paper 'A' and it states a fact with a reference back to paper 'B', but I cannot access paper 'B', If I can't find another option then sometimes I just accept the fact stated by 'A' and cite 'B' as the source. I've never been certain about this type of by-proxy sourcing. Similarly, I've cited Chem Rev articles when I cannot access them, but only when they are unambiguously relevant (name reactions, for instance). I have no access to pay-walled content beyond the Wikipedia Library, nor any SciFinder etc. I feel that I have become very good at finding sources by other means, but it can still be a challenge to write a new overview. Mostly it's just very slow, I've working on organophosphate for months and I'm still not done with it. What I will say is that I think it's better then when started. There are lots of pages like that, where if not good, they can at least be made not bad. --Project Osprey (talk) 20:32, 23 June 2024 (UTC)

A plea for help with the short list of good (and legal) open source reference works (which I put on our project page). Should we put this list in our Manual of Style (would it be ignored there?), should we leave it on the project page, should we do something else with this list? --Smokefoot (talk) 22:50, 23 June 2024 (UTC)

Our project page is a good place for it. The list is a bit out of scope for a manual of style. Reacting to Project Osprey's A references B, you must be very careful. You could just reference A. But in a significant number of cases I have found that the A paper misrepresents B, so it is best to make sure what it says before using it as a reference. Also thanks to Smokefoot for recommending Shriver & Atkin's Inorganic Chemistry 5th ed, which can also be found to read on archive.org. It is 14 years old. If this is entirely legal, then it would be worth a link too. Graeme Bartlett (talk) 10:35, 24 June 2024 (UTC)

Good article reassessment for Nature

Nature has been nominated for a good article reassessment. If you are interested in the discussion, please participate by adding your comments to the reassessment page. If concerns are not addressed during the review period, the good article status may be removed from the article. Z1720 (talk) 20:11, 26 June 2024 (UTC)

Arsenic trioxide dimer?

In Wikipedia:Featured article candidates/1858 Bradford sweets poisoning/archive1, I objected to the image File:As4O6-molecule-from-arsenolite-xtal-3D-balls.png being labeled as "arsenic trioxide" and suggested it might be a dimer. But I'm not sure if that's actually the correct term for this kind of structure. Could somebody with better chemistry-fu than me take a look? RoySmith (talk) 01:07, 16 July 2024 (UTC)

According to Arsenic trioxide it seems like it forms dimers at temperatures below 800 degrees Celsius, so for these circumstances it is accurate (assuming that the Wikipedia article is correct, of course). There are also polymeric allomorphs. Jo-Jo Eumerus (talk) 06:56, 16 July 2024 (UTC)

Under standard conditions it would appear to exist in the claudetite forms, so maybe switch one of those? --Project Osprey (talk) 08:59, 16 July 2024 (UTC)

Names of chemical formula with anions

Are there any names of chemical formulas with anions in the examples of Pentagonal pyramidal molecular geometry? I'm not expert at chemistry, but I probably need explanation. For example, can I called IOF²⁻
₅ as "iodine pentafluoride with two anions"? Dedhert.Jr (talk) 13:37, 18 July 2024 (UTC)

IOF
₅ is not iodine pentafluoride because there is an additional oxygen atom - it's iodosyl pentafluoride. IOF²⁻
₅ can be referred to as iodosyl pentafluoride dianion. Marbletan (talk) 14:53, 18 July 2024 (UTC)

Many thanks. Dedhert.Jr (talk) 01:26, 19 July 2024 (UTC)

@Dedhert.Jr Note that the dianion you are interested in is not the same thing as iodosyl pentafluoride. To take a simpler example, we have sulfur trioxide SO₃ and the sulfite dianion SO²⁻
₃. As these articles explain, the shapes of these are quite different and the latter has two more electrons than the former: you can have a sample of sulfur trioxide as-is but the sulfite can only exist in combination with a counterion, as a salt. So, returning to IOF²⁻
₅, the article in which it was first characterised is doi:10.1021/ja980057+ and you'll see that this was as its tetramethylammonium salt. Naming the dianion is complicated according to IUPAC conventions, and I don't suggest you try! The relevant guidance would be the Red Book, which you can download, but if you are not an expert, I would recommend just sticking to the molecular formula. Mike Turnbull (talk) 10:08, 19 July 2024 (UTC)

@Michael D. Turnbull Many thanks as well. I'm thinking about the GAN Pentagonal pyramid in which I wrote the molecule with a pentagonal pyramid structure. The name of the chemical formula is technically needed if I want to avoid WP:TECHNICAL. Dedhert.Jr (talk) 13:20, 19 July 2024 (UTC)

@Dedhert.Jr I'm not sure that guideline is very useful here! I think that the anion might formally be called pentafluoro-oxo-iodate based on the related X-ray structure of the hexafluoro one. However, Pubchem call the hexa compound hexafluoro(oxido)-λ⁷-iodane, which means this one would be pentafluoro(oxido)-λ⁶-iodane and that's more in tune with the Red Book. You need an expert in inorganic nomenclature: maybe User:Double sharp could oblige. Incidentally, a better citation for the GAR than your current Baran one is his 2008 review at doi:10.1016/j.jfluchem.2008.06.016, which talks about all sorts of coordination geometries. I added that cite to the chemistry article today after replying here. Mike Turnbull (talk) 16:17, 19 July 2024 (UTC)

I have to agree with Michael D. Turnbull here: it's probably going to be easier to understand the formula than the name! I think he's given you the correct substitutive name indeed, but probably the additive name is more familiar: pentafluoridooxidoiodate(2−). Double sharp (talk) 03:30, 20 July 2024 (UTC)

@Double sharp, @Michael D. Turnbull Many thanks again. However, are there any chemical compound with pentagonal pyramidal structure other than IOF²⁻
₅? In GA square pyramid, it mentions the name of chemical compound with square pyramidal structure. Since both articles are mathematics topics, I cannot add the chemical compound rather than its name; or we can see another in Triaugmented triangular prism. Dedhert.Jr (talk) 04:40, 20 July 2024 (UTC)

@Dedhert.Jr: This Chemistry Stack Exchange comment contains links to papers describing such compounds. Double sharp (talk) 04:44, 20 July 2024 (UTC)

RfC: On discovery of the 23 nonmetals

Should this content on the discovery of the 23 nonmetals be removed from the nonmetal article?

RfC is here. --- Sandbh (talk) 13:39, 23 July 2024 (UTC)

Access to ACS journals via The Wikipedia Library

Currently, the TWL offers comprehensive access to literature ressources relevant to chemistry. The likely most important collection of scientific journals in the field of chemistry, which also partially covers neighboring disciplines including physics, biology, materials science or nutritional science, is published by the American Chemical Society (ACS). Unfortunately, TWL does not offer access to the ACS journals. In the Wikimedia Phabricator's TWL area the potential subscription to the ACS journal collection is currently listed under "Prospects". The number of Wikipedia authors supporting such a subscription is apparently relevant to the prioritization of new TWL subscriptions. Therefore, my request would be that anyone, who is also interested in getting access to the ACS journals, supports the proposal to subscribe to the ACS journals. For this purpose, log in to TWL, go the "suggest a collection" page (https://wikipedialibrary.wmflabs.org/suggest/), scroll down to the ACS entry and click on "Support". This doesn't cost much... Thanks for any support! Espresso robusta (talk) 13:42, 4 August 2024 (UTC)

@Espresso robusta Great suggestion! Unfortunately, the upvotes are currently only at 30, which still places us quite low in the list. Mike Turnbull (talk) 16:50, 4 August 2024 (UTC)

@Espresso robusta thanks for suggesting! I have an ACS membership so get some access that way but for scientists who don't have access via industry or university it would be a great resource. 34 upvotes isn't too bad for a niche area... Nnev66 (talk) 17:03, 5 August 2024 (UTC)

Potassium hexacyanidoferrate(III)‎... wha?

This tortured IUPAC nomenclature. Unfortunate. Practicing chemists do not use this term. --Smokefoot (talk) 16:51, 13 June 2024 (UTC)

Any time I've seen this out in the wild (I'm sure I have somewhere) it's been potassium ferricyanide which is where it was just moved from. If it really had to be at the IUPAC name, shouldn't it get moved to Tripotassium;iron(3+);hexacyanide? There's a reason the water page isn't called Oxidane.

Also possibly relevant, Potassium trichloridocuprate(II). Recon rabbit 20:20, 13 June 2024 (UTC)

Even Potassium hexacyanoferrate(III) was much more commonly used. I have moved the page back to potassium ferricyanide which is more commonly used by about a factor of 1000. Wikipedia policy is to use the most frequently used name rather than official (here closest to IUPAC). Letting @JWBE: know about reversion of the move. Graeme Bartlett (talk) 22:48, 13 June 2024 (UTC)

Greetings, Smokefoot! I have also found several instances of this, like with DIBAL and Red-Al. I am pretty sure that it would be fine to refer to DIBAL as, well, DIBAL. However, do you think it appropriate to refer to Red-Al as Red-Al due to it being a trade name? Pygos (talk) 13:19, 14 August 2024 (UTC)

The structure of tantalum pentoxide

File:Kristallstruktur_Triuranoctoxid.png

Tantalum pentoxide (Ta₂O₅) currently shows the crystal structure for Triuranium octoxide (U₃O₈). We frequently use use crystallographic archetypes in this way, but looking closer, I don't think this one is right. The stoichiometries don't add up, the uranium compound is mixed valance (V,VI) but the Tantalum one isn't. The imagine has been used this way on all the non-English pages as well. Project Osprey (talk) 15:38, 16 August 2024 (UTC)

Let me see what I can find. Usually Ben Mills does these images. --Smokefoot (talk) 16:03, 16 August 2024 (UTC)

Ethanol vs. methanol

Hello WikiProject Chemistry! Could I get someone's eyes on 2016 Irkutsk mass methanol poisoning to make sure I've characterized these two substances correctly? The article is currently at WP:FAC. (And would anyone be game to stage and take a comparison photo of the two to demonstrate how similar they appear...?) Ed ^{[talk] [OMT]} 14:59, 13 August 2024 (UTC)

I have stock of both chemicals around, I can easily do a photo of each in side-by-side labeled vials later today. We've generally shied away from those on chemical articles (so I'm not surprised we don't already have each in c:Category:Methanol and c:Category:Ethanol), since they're both identical appearance clear colorless liquids. But obviously that comparison is relevant here. DMacks (talk) 15:23, 13 August 2024 (UTC)

@Dmacks: Thank you so much! A photo was a great suggestion from a reviewer at the FAC and will help to communicate how these people unknowingly drank methanol. Ed ^{[talk] [OMT]} 15:31, 13 August 2024 (UTC)

@DMacks: fixing ping. Ed ^{[talk] [OMT]} 17:04, 13 August 2024 (UTC)

I actually think that showing ethanol and methanol side-by-side is a great idea because (not despite) them being both identical appearance clear colorless liquids. That would illustrate rather beautifully why the poisonings happen. Jo-Jo Eumerus (talk) 07:23, 14 August 2024 (UTC)

They also have similar odours, which is rather harder to show in an article here! Concluding that the similarity in appearance was the reason for the poisonings would be original research: those who drank the stuff knew they had purchased bootleg "bath oil" to avoid the tax on alcohol. Mike Turnbull (talk) 12:01, 14 August 2024 (UTC)

Sorry for the delay, @The ed17 and Jo-Jo Eumerus:! Here you go: File:Methanol ethanol vials.jpg. Mike Turnbull makes a good point, that there should be a cited statement that they cannot be distinguished by appearance. This is mentioned without cite in methanol#Toxicity, and surprisingly not even mentioned at all in methanol toxicity. The statement in the FAC article is "Methanol is cheaper than ethanol, and the two cannot readily be distinguished." but the given NYTimes ref does not appear to mention anything related to that second clause. DMacks (talk) 06:28, 18 August 2024 (UTC)

@Michael D. Turnbull and DMacks: Oof. So I dug into that and found the phrase was added just a day after the article was created, and I never noticed that the info didn't match up with the attached ref. Thank you for your diligence, and to Dmacks for the photo. I've added a Britannica reference to replace it -- I was surprised to find that it wasn't the easiest thing to find a replacement ref for. Ed ^{[talk] [OMT]} 23:35, 18 August 2024 (UTC)

Thanks for tracking down a source! There's so much common knowledge that isn't stated explicitly in discoverable RS:( DMacks (talk) 23:38, 18 August 2024 (UTC)

Carbocation business

I am contemplating changes affecting at least 4 articles. The evolving plans are described at Talk:Carbocation#Merge proposal:

relocate most, not all, carbenium ion (R₃C⁺) content from carbocation to carbenium ion article.
relocate most, not all, carbonium ion (R₅C⁺) content from carbocation to the carbonium ion article with a sections on some individual nonclassical carbocations such as 2-norbonyl cation and many others.
convert carbocation into a concise summary of these two kinds of cations, keep the "history" and the "nomenclature".
move 2-Norbornyl cation to Norbornyl cation debate to incorporate all that history. This debate, once a "thing", was settled when the X-ray structure was announced in 2013. It is doubtful that many readers want to wade through that history. 2-Norbornyl cation would redirect to carbonium ion#2-Norbornyl cation together with related cations such as homoallyl cation and cyclopropyl methyl cation. I am not an expert on these topics in case you are wondering.--Smokefoot (talk) 16:34, 31 August 2024 (UTC)

I would appreciate the "debate" to be a separate article, as it gets difficult to read what the current beliefs about it are with that massive history and theory included. But I think 2-Norbornyl cation has enough material to be its own article. Graeme Bartlett (talk) 04:48, 1 September 2024 (UTC)

I like it! For (3), don't forget to include vinyl cation, and a mention of the false teaching tool of drawing acylium ions with a carbonyl-carbocation resonance form (see doi:10.1021/ed5002152). DMacks (talk) 06:50, 1 September 2024 (UTC)

Sounds good. There is a problem with the lead in carbenium ion "But IUPAC confuses...." which is only referenced to the IUPAC definition. This needs to be re-written carefully to avoid being WP:OR. Carbocation#Definitions may clear this up. Mike Turnbull (talk) 15:03, 1 September 2024 (UTC)

I will follow the suggestions above. Also, this thing showed up: nonclassical ion, which could be a home for relatives of 2-Norbornyl cation-like species or could be redirected to carbocation. And then Pyramidal carbocation. Someone might inspect (remove???) the extensive calculations and theory, we dont do that kind of analysis typically.--Smokefoot (talk) 15:42, 1 September 2024 (UTC)

If you think you can improve it then be bold. If you have reservations, then maybe do the new pages in a sandbox and we can see later? Some comments: (1) We normally use the simplest example of a functional group as an archetype for our descriptions, but methenium basically doesn't exist. It might be easier to use the t-butyl cation. Butylation is big business, so it is relevant and there may be better references. (2) The alkylation of alpha-olefins to give linear alkylbenzene illustrates the behaviour of secondary carbenium ions (i.e. they clearly exist, but the the charge moves freely up and down chain, giving a range of products). The Wagner–Meerwein rearrangement for the industrial production of vitamin E (not shown on our page) is a nice example of this willingness to rearrange being put to practical use. The presence of a 3c-2e bond in some protonated alkenes (ethanium) seems to be at odds with Markovnikov's rule as it implies the cations can be terminal-ish, I'm not sure what the reality is there (do we ever see any completely linear alkylbenzenes?) --Project Osprey (talk) 21:41, 1 September 2024 (UTC)

Guidelines on chemistry solubility?

I originally posted this at the help desk: Wikipedia:Help desk/Archives/2024 September 1 - Wikipedia but was recommended to post this here.

On the MoS for line equations it merely says "Do not include phase definitions unless they are absolutely essential". Normally, the states of matter as written as, for example, AgCl(s), but on the silver chloride page the precipitate is written as a down arrow for 2 equations and with a subscript for the remaining. Does Wikipedia have a preferred style?

Also, on some pages, like silver phosphate, as well as the main article for solubility product, the solubility product is written with units at the end of it, when it is usually treated as a dimensionless quantity. Is there a preferred style? SecretSpectre (talk) 06:30, 5 September 2024 (UTC)

You have already found WP:Manual_of_Style/Chemistry#Line_equations, which is where any agreement on the preferred style is likely to have been recorded. You can suggest/discuss additions to the guidelines right here, if you like. IMO if you are making a proposal to fix on a preferred style, you also need some way to identify by a search where we would need to change existing articles in the "wrong" style. Mike Turnbull (talk) 12:13, 5 September 2024 (UTC)

The first question (states) is actually two ideas. One idea is whether to use the parenthetical letter vs up/down-arrow in an equation based on the merits or context of that equation. My position is that both are acceptable, but the arrow emphasizes that there is a phase change (such as "becoming a solid" or "coming out of solution") vs just being a solid. The other idea is the general goal of Wikipedia:Consistency, such as using the same thing within any one article. But I think consistency should always be secondary to clear and correct meaning, so I'm having trouble thinking of a time that both would be equally appropriately meaningful and still worth including. DMacks (talk) 18:05, 5 September 2024 (UTC)

Featured article review of Heavy metal (elements)

I have started a Featured article review of Heavy metal (elements), please follow the link to the source. Based upon reading the sources too many did not validate; Johnjbarton also had some serious criticisms. Ldm1954 (talk) 23:28, 6 September 2024 (UTC)

N.B., the main page is Wikipedia:Featured article review#Heavy metal (elements), the link above goes directly to a page just on this FAR. Ldm1954 (talk) 00:20, 7 September 2024 (UTC)

Errors in a Periodic Table on Wikimedia Commons

It was brought to my attention that File:Periodic Table Of Elements Black And White.svg on Commons has multiple errors. There has been a comment on the file's talk page about the wrong atomic numbers since 2020. Does anyone know how to either get the file fixed or deleted? See below for comments copied from the file's talk page.

The elements Te, and Ir -> Hg all have the wrong atomic numbers assigned to them. Griceylipper (talk) 13:57, 12 December 2020 (UTC)

I noticed Thallium has "TI" (capital T, Capital I) as its symbol, not Tl (capital T, lower case l) - look at Chlorine (Cl) or Aluminum (Al) to see what a lower case "l" looks like. Ruhrfisch (talk) 18:37, 6 September 2024 (UTC)

Thanks, - Ruhrfisch _><>°^° 18:42, 6 September 2024 (UTC)

@Ruhrfisch That file doesn't seem to be used in any article in any language version of Wikipedia (see its Commons page) and the uploader hasn't made any contributions there since 2016 when it was uploaded. You can nominate the file for deletion using the menu on the left of its file page on Commons. Mike Turnbull (talk) 19:26, 6 September 2024 (UTC)

@Griceylipper Apologies, I see it was you who made the original post, not Ruhrfisch. Mike Turnbull (talk) 19:28, 6 September 2024 (UTC)

For now I have added the Disputed chem template to the page so that others are warned about the problem and are less likely to attempt to use it. File:Periodic Table Of Elements.svg by the same uploader had similar issues, but most of the errors have already been corrected (Te still has the wrong atomic number though, so I've marked that one as disputed too). Marbletan (talk) 19:34, 6 September 2024 (UTC)

I suggest just nominating both for deletion, I think there are enough others. Ldm1954 (talk) 20:33, 6 September 2024 (UTC)

Thanks everyone - I have nominated the Commons file for deletion, here: c:Commons:Deletion requests/File:Periodic Table Of Elements Black And White.svg. - Ruhrfisch _><>°^° 01:27, 7 September 2024 (UTC)

The link is c:Commons:Deletion_requests/File:Periodic_Table_Of_Elements_Black_And_White.svg Mike Turnbull (talk) 10:18, 7 September 2024 (UTC)

Thanks, I fixed the link in my original comment. I've not been very active recently and did not know the "c:" prefix trick. Thanks again, - Ruhrfisch _><>°^° 00:45, 8 September 2024 (UTC)

Wikipedia:Categories for discussion/Log/2024 September 15#Category:Chemical looping technologies

Hi! The regulars are CFD are not chemistry experts, so we would really appreciate your input at Wikipedia:Categories for discussion/Log/2024 September 15#Category:Chemical looping technologies. No knowledge of CFD policies/procedures necessary – the participants have a question about whether Chemical looping combustion and Chemical looping reforming and gasification belong in Category:Chemical process engineering or Category:Chemical processes. Best, House Blaster (talk • he/they) 02:03, 15 September 2024 (UTC)

Made-up chemical names!

Hi! I wanted to let you all know of something I came across while browsing today. I removed multiple "alternate names" for very common chemicals that I believe are completely made up, all added in 2023 by the same IP editor:

"Benzane" for Cyclohexa-1,3-diene
"Phenane" and "Phenylene hydride" for Benzene
"Acetoic acid" and "Oxoacetal" for Pyruvic acid

None of these names appeared in any legitimate chemical context that I could find aside from a couple of obvious typos, so I went ahead and removed them, but that user has some other questionable naming edits that I wasn't 100% sure about and it seems like there may be others doing the same thing (I think this is likely the same person).

Thanks, Cystathionine (talk) 07:11, 17 September 2024 (UTC)

They would be in the category of WP:Original research. Did any get created as redirects? Graeme Bartlett (talk) 09:03, 17 September 2024 (UTC)

The good news is that they're all simple article edits — no redirects — by one or more well-meaning but unhelpful editors (no malicious vandalism). The bad news is that there appear to be other IPs in this cluster. Cystathionine found 42.117.40.173 and 115.74.10.44, and 115.74.4.110 looks like another one. Pattern seems to be edits in early-mid 2023, with no commit messages, by IPs that geolocate to Vietnam (albeit Hanoi and Vũng Tàu, so they might not be exactly the same editor).

Here's a list of edits from the first two IPs that hadn't been reviewed yet — I'd appreciate if someone else could have a look over my doco here and clean up any remaining mess:

Dibenzene in Biphenyl — seems incorrect to me, reverted.
Xenene in Biphenyl — valid, kept.
Benzoylic acid and Carboxylbenzene in Benzoic acid — both names appear to be rare but valid, kept.
Dicarboxylbenzene, Carboxylbenzoic acid, 1,2-Phenylenedicarboxylic acid, Phenylene-1,2-dicarboxylic acid in Phthalic acid — 1,2-dicarboxylbenzene would be valid (but is not what they added), other two aren't really used, reverted.
Carbonous acid in Formic acid — not just invalid, but refers to a different compound, reverted; have also removed Isocarbonous acid (added in 13:41, 5 April 2017) as this isn't in PubChem or ChemSpider (or anything else either); could also have added back Aminic acid (rare but valid) but elected not to.
Acetocarboxylic acid in 00:43, 3 February 2023 and 00:44, 3 February 2023 (as Acetonoic acid already removed, as well as Acetoic acid, Oxoacetol in 03:39, 4 February 2023 already removed) — invalid, reverted. Also noticed Acetoic acid had been removed from the chembox but not the article body — fixed.
Phosphinol in Phosphinous acid — invalid, reverted.
Their edits for Lead(IV) acetate and Lead(IV)_chloride actually seem to be OK
Plumbous acid in Lead(II) hydroxide — invalid, reverted.
Pentylene (and other changes) in Pentene — perhaps technically correct but unhelpful, reverted.

I haven't had a proper look at the ones in 115.74.4.110 but I think most (though not all) of these need to be reverted too — would someone else be able to have a look over those? Preimage (talk) 14:20, 17 September 2024 (UTC)

@Cystathionine Well spotted. ChemSpider and Pubchem both have extensive lists of synonyms for chemical names. If any of the ones the IPs added aren't there, they should certainly be removed and even if they are present in those databases, Wikipedia's chemboxes don't need to include every possible alternate name. Mike Turnbull (talk) 13:16, 17 September 2024 (UTC)

Google Patents turns up a couple East Asian patents which Google translates as using "acetoic acid"; compare e.g. TW I462957B vs US 8952099B2 - though espacenet does not use "acetoic acid" in its own machine-translated version of the Taiwanese patent. As both IP addresses mentioned are from Vietnam, I wonder if this is either a regional form, or a Google Translate issue. In either case I don't think it merits mention on English Wikipedia. Fishsicles (talk) 14:17, 17 September 2024 (UTC)

I'd also note that as best I can correlate the two translations, "acetoic acid" does not appear to refer to pyruvic acid, which probably pushes it more in line with a possible MTL issue. Fishsicles (talk) 14:23, 17 September 2024 (UTC)

Chemical formulas on Wikidata

During a discussion on Wikidata (see https://www.wikidata.org/wiki/Wikidata:Property_proposal/chemical_formula), it came out pages like https://en.wikipedia.org/wiki/C15H20O4 would benefit from the proposal, maybe of interest for people here to add their opinions? AdrianoRutz (talk) 08:40, 29 August 2024 (UTC)

{{ping| AdrianoRutz} What exactly is the proposal? These discussions seem to be dominated by editors who have little cred in chemical editing.--Smokefoot (talk) 13:21, 29 August 2024 (UTC)

It looks like the proposal is to convert every chemical name into a formula. As shown in the example: 2-hydroxy-5-octanoylbenzoic acid (Q209407), abscisic acid (Q332211), and Santonic acid (Q7420590) will all be changed to be defined as C₁₅H₂₀O₄ (Q129998552). This seems like a bad idea. It's noted in the first comment that the general formula would be "isotope-agnostic", but subclasses could be made for each isotope. Never mind what the implications are for structural isomers. I could be completely misconstruing what the proposal is though because it isn't clear to me either. Looking at it again it appears the proposal is to, instead of defining each chemical's formula as a unique string, defining a specific item for every single chemical formula that can be shared between structural isomers and isotopes. Recon rabbit 15:30, 29 August 2024 (UTC)

The proposal is about switching the actual way chemical formulae are modelled internally in Wikidata. Currently, they are strings and not items and this comes with many disadvantages for efficient querying and data redundancy. Having them as items on Wikidata would allow more refined queries (such as "give me all chemical entities that contain X carbon, Y hydrogen and Z oxygen", for example) and drastically reduce the number of "mass" statements needed as these could move from the chemical entity item to the formula item and thus help maintainers focus on less, higher quality masses.

I will pass above you "street cred" statement. No place for such things, but I invite you to look at the Chemistry project on Wikidata and see the beautiful things some fantastic contributors are doing. AdrianoRutz (talk) 09:33, 23 September 2024 (UTC)

This is also highly relevant to Wikipedia, as some existing pages about chemical formulas (https://en.wikipedia.org/wiki/C15H20O4) linked to different chemical entities could heavily benefit from it, or even the chem info box. AdrianoRutz (talk) 09:36, 23 September 2024 (UTC)